PMC:7571312 / 58168-59224 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T493","span":{"begin":250,"end":251},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T494","span":{"begin":900,"end":902},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T495","span":{"begin":937,"end":942},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}

{"project":"LitCovid-PD-CHEBI","denotations":[{"id":"T351","span":{"begin":72,"end":79},"obj":"Chemical"},{"id":"T35648","span":{"begin":80,"end":93},"obj":"Chemical"},{"id":"T14380","span":{"begin":80,"end":82},"obj":"Chemical"},{"id":"T47527","span":{"begin":94,"end":102},"obj":"Chemical"},{"id":"T17117","span":{"begin":106,"end":112},"obj":"Chemical"},{"id":"T89113","span":{"begin":113,"end":118},"obj":"Chemical"},{"id":"T12500","span":{"begin":122,"end":125},"obj":"Chemical"},{"id":"T40611","span":{"begin":155,"end":168},"obj":"Chemical"},{"id":"T53583","span":{"begin":155,"end":160},"obj":"Chemical"},{"id":"T85901","span":{"begin":161,"end":168},"obj":"Chemical"},{"id":"T87477","span":{"begin":186,"end":206},"obj":"Chemical"},{"id":"T31167","span":{"begin":188,"end":206},"obj":"Chemical"},{"id":"T53497","span":{"begin":202,"end":206},"obj":"Chemical"},{"id":"T3423","span":{"begin":326,"end":334},"obj":"Chemical"},{"id":"T369","span":{"begin":335,"end":350},"obj":"Chemical"},{"id":"T64316","span":{"begin":398,"end":400},"obj":"Chemical"},{"id":"T371","span":{"begin":415,"end":419},"obj":"Chemical"},{"id":"T372","span":{"begin":448,"end":450},"obj":"Chemical"},{"id":"T9840","span":{"begin":474,"end":476},"obj":"Chemical"},{"id":"T53167","span":{"begin":500,"end":502},"obj":"Chemical"},{"id":"T48220","span":{"begin":540,"end":542},"obj":"Chemical"},{"id":"T80277","span":{"begin":592,"end":594},"obj":"Chemical"},{"id":"T57111","span":{"begin":618,"end":620},"obj":"Chemical"},{"id":"T378","span":{"begin":644,"end":646},"obj":"Chemical"},{"id":"T68385","span":{"begin":670,"end":672},"obj":"Chemical"},{"id":"T89225","span":{"begin":696,"end":698},"obj":"Chemical"},{"id":"T381","span":{"begin":715,"end":717},"obj":"Chemical"},{"id":"T42226","span":{"begin":786,"end":788},"obj":"Chemical"},{"id":"T383","span":{"begin":805,"end":807},"obj":"Chemical"},{"id":"T62942","span":{"begin":824,"end":826},"obj":"Chemical"},{"id":"T385","span":{"begin":900,"end":902},"obj":"Chemical"},{"id":"T5217","span":{"begin":980,"end":983},"obj":"Chemical"},{"id":"T387","span":{"begin":989,"end":992},"obj":"Chemical"}],"attributes":[{"id":"A5638","pred":"chebi_id","subj":"T351","obj":"http://purl.obolibrary.org/obo/CHEBI_32772"},{"id":"A61347","pred":"chebi_id","subj":"T351","obj":"http://purl.obolibrary.org/obo/CHEBI_44520"},{"id":"A95276","pred":"chebi_id","subj":"T35648","obj":"http://purl.obolibrary.org/obo/CHEBI_51611"},{"id":"A91934","pred":"chebi_id","subj":"T14380","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A18912","pred":"chebi_id","subj":"T47527","obj":"http://purl.obolibrary.org/obo/CHEBI_23019"},{"id":"A53726","pred":"chebi_id","subj":"T17117","obj":"http://purl.obolibrary.org/obo/CHEBI_32630"},{"id":"A34175","pred":"chebi_id","subj":"T17117","obj":"http://purl.obolibrary.org/obo/CHEBI_37904"},{"id":"A97897","pred":"chebi_id","subj":"T89113","obj":"http://purl.obolibrary.org/obo/CHEBI_46882"},{"id":"A50759","pred":"chebi_id","subj":"T12500","obj":"http://purl.obolibrary.org/obo/CHEBI_46629"},{"id":"A48524","pred":"chebi_id","subj":"T40611","obj":"http://purl.obolibrary.org/obo/CHEBI_31328"},{"id":"A31636","pred":"chebi_id","subj":"T53583","obj":"http://purl.obolibrary.org/obo/CHEBI_41264"},{"id":"A16971","pred":"chebi_id","subj":"T85901","obj":"http://purl.obolibrary.org/obo/CHEBI_30089"},{"id":"A94175","pred":"chebi_id","subj":"T85901","obj":"http://purl.obolibrary.org/obo/CHEBI_47622"},{"id":"A98318","pred":"chebi_id","subj":"T87477","obj":"http://purl.obolibrary.org/obo/CHEBI_30747"},{"id":"A48743","pred":"chebi_id","subj":"T31167","obj":"http://purl.obolibrary.org/obo/CHEBI_23134"},{"id":"A53112","pred":"chebi_id","subj":"T31167","obj":"http://purl.obolibrary.org/obo/CHEBI_51967"},{"id":"A28328","pred":"chebi_id","subj":"T53497","obj":"http://purl.obolibrary.org/obo/CHEBI_37527"},{"id":"A42689","pred":"chebi_id","subj":"T3423","obj":"http://purl.obolibrary.org/obo/CHEBI_17790"},{"id":"A32757","pred":"chebi_id","subj":"T369","obj":"http://purl.obolibrary.org/obo/CHEBI_15767"},{"id":"A16378","pred":"chebi_id","subj":"T64316","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A4049","pred":"chebi_id","subj":"T371","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"},{"id":"A13723","pred":"chebi_id","subj":"T372","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A75478","pred":"chebi_id","subj":"T9840","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A44305","pred":"chebi_id","subj":"T53167","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A79384","pred":"chebi_id","subj":"T48220","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A94798","pred":"chebi_id","subj":"T80277","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A79780","pred":"chebi_id","subj":"T57111","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A98260","pred":"chebi_id","subj":"T378","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A48497","pred":"chebi_id","subj":"T6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the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}

{"project":"LitCovid-sentences","denotations":[{"id":"T372","span":{"begin":0,"end":266},"obj":"Sentence"},{"id":"T373","span":{"begin":267,"end":397},"obj":"Sentence"},{"id":"T374","span":{"begin":398,"end":945},"obj":"Sentence"},{"id":"T375","span":{"begin":946,"end":1021},"obj":"Sentence"},{"id":"T376","span":{"begin":1022,"end":1056},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}

{"project":"LitCovid-PD-HP","denotations":[{"id":"T10","span":{"begin":989,"end":992},"obj":"Phenotype"}],"attributes":[{"id":"A10","pred":"hp_id","subj":"T10","obj":"http://purl.obolibrary.org/obo/HP_0001644"}],"text":"Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1296","span":{"begin":186,"end":206},"obj":"Chemical"},{"id":"1297","span":{"begin":326,"end":334},"obj":"Chemical"},{"id":"1298","span":{"begin":335,"end":350},"obj":"Chemical"},{"id":"1299","span":{"begin":962,"end":974},"obj":"Chemical"},{"id":"1300","span":{"begin":980,"end":983},"obj":"Chemical"},{"id":"1301","span":{"begin":989,"end":992},"obj":"Chemical"},{"id":"1302","span":{"begin":994,"end":995},"obj":"Chemical"},{"id":"1303","span":{"begin":1013,"end":1014},"obj":"Chemical"},{"id":"1304","span":{"begin":1029,"end":1030},"obj":"Chemical"},{"id":"1305","span":{"begin":1048,"end":1049},"obj":"Chemical"}],"attributes":[{"id":"A1296","pred":"tao:has_database_id","subj":"1296","obj":"MESH:C040768"},{"id":"A1297","pred":"tao:has_database_id","subj":"1297","obj":"MESH:D000432"},{"id":"A1298","pred":"tao:has_database_id","subj":"1298","obj":"MESH:D008752"},{"id":"A1301","pred":"tao:has_database_id","subj":"1301","obj":"MESH:D008752"},{"id":"A1302","pred":"tao:has_database_id","subj":"1302","obj":"MESH:D002244"},{"id":"A1303","pred":"tao:has_database_id","subj":"1303","obj":"MESH:D009584"},{"id":"A1304","pred":"tao:has_database_id","subj":"1304","obj":"MESH:D002244"},{"id":"A1305","pred":"tao:has_database_id","subj":"1305","obj":"MESH:D009584"}],"namespaces":[{"prefix":"Tax","uri":"https://www.ncbi.nlm.nih.gov/taxonomy/"},{"prefix":"MESH","uri":"https://id.nlm.nih.gov/mesh/"},{"prefix":"Gene","uri":"https://www.ncbi.nlm.nih.gov/gene/"},{"prefix":"CVCL","uri":"https://web.expasy.org/cellosaurus/CVCL_"}],"text":"Following the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}